"If financial services and healthcare are 10 years behind everybody else from a technology adoption standpoint, insurance distribution is usually 10 years behind that." - Will Johnson

My guest this week is Will Johnson, Founder and CEO of Gyde, who is building what he calls the first "AI-native" insurance brokerage. After spending a decade at Oscar Health, Will realized that while brokers are the critical "entry point to care," they are operating without the infrastructure needed to scale in the modern era.

In this episode, we define exactly what "AI-native" means for an agency. It isn't just about buying software; it's a new holding company model that acquires agencies to deploy AI infrastructure - automating renewals and client service to effectively "triple the capacity" of the best brokers.

We dive deep into the difference between the traditional "asset aggregation" model (roll-ups) and Gyde’s "partner activation" model. Will also shares why Gyde raised a Series A just 14 weeks after launching and his moonshot vision to converge health insurance and wealth management into a single advisory role.

If you are an agency owner feeling the ceiling of growth, this episode maps out what the next generation of distribution looks like.

Thank you to our 2026 sponsors!

ParetoHealth: ParetoHealth empowers midsize employers with a long-term solution to reduce volatility and lower overall health benefits costs. Visit ParetoHealth.com to learn more.

Samaritan Fund: A program that connects those who need help to the support they need. We are proud to offer the Samaritan Fund Program. Visit SamaritanFundProgram.com to learn more.

Vālenz Health: We're Vālenz Health, your partner in improving health literacy, reducing plan spend, and delivering high-value healthcare. Visit ValenzHealth.com to learn more.

Imagine360: Imagine360 helps self-funded employers save on healthcare with smarter health plans. Cut expenses by 20-30% with custom solutions. Contact us today at Imagine360.com.

Chapters:

(00:00:00) What is an "AI-Native" Brokerage?

(00:03:11) Will’s Journey: 10 Years at Oscar Health

(00:07:10) The Infrastructure Gap in Distribution

(00:12:27) Why Acquisition? The Case for Economic Alignment

(00:23:22) The Tech Stack: Automating Renewals & Service

(00:27:32) AI as a "Capacity Amplifier" vs. Replacement

(00:37:22) The Anti-Rollup: "Partner Activation" vs. "Asset Aggregation"

(00:46:12) Branding: Powered by Guide vs. Becoming Guide

(00:49:49) Raising a Series A in 14 Weeks

Key Links for Social:

@SelfFunded on YouTube for video versions of the podcast and much more - https://www.youtube.com/@SelfFunded

Listen/watch on Spotify - https://open.spotify.com/show/1TjmrMrkIj0qSmlwAIevKA?si=068a389925474f02

Listen on Apple Podcasts - https://podcasts.apple.com/us/podcast/self-funded-with-spencer/id1566182286

Follow Spencer on LinkedIn - https://www.linkedin.com/in/spencer-smith-self-funded/

Follow Spencer on Instagram - https://www.instagram.com/selffundedwithspencer/

"I stopped doing what I didn't want to do anymore. It’s not hard to stop doing something you don't want to do... I didn't want to drink anymore." - Chris Leverett

In this incredibly vulnerable and powerful episode, we step away from the usual technical discussions of self-funding and insurance captives to tackle a pervasive, often silent issue in our industry: addiction and sobriety.

My guest is Chris Leverett, Executive Vice President and Managing Director of Employee Benefits at TexCap Insurance. While Chris is a veteran in the benefits space, today he shares his personal testimony of battling high-functioning alcoholism while trying to maintain a career, a marriage, and a family.

Chris opens up about the "boiling frog" effect of social drinking in the business world, the crushing weight of keeping up appearances, and the terrifying rock-bottom moments, including a lapse in insurance coverage during his daughter's premature birth, that finally led him to seek help.

We discuss the freedom found in admitting powerlessness, how he replaced the "monster" of addiction with the discipline of Ironman triathlons, and how to navigate the alcohol-heavy social scene of insurance events without losing your edge.

If you or someone you know is struggling in silence, this episode provides a blueprint for finding hope, help, and a better life on the other side.

Thank you to our 2026 sponsors!

ParetoHealth: ParetoHealth empowers midsize employers with a long-term solution to reduce volatility and lower overall health benefits costs. Visit ParetoHealth.com to learn more.

Samaritan Fund: A program that connects those who need help to the support they need. We are proud to offer the Samaritan Fund Program. Visit SamaritanFundProgram.com to learn more.

Vālenz Health: We're Vālenz Health, your partner in improving health literacy, reducing plan spend, and delivering high-value healthcare. Visit ValenzHealth.com to learn more.

Imagine360: Imagine360 helps self-funded employers save on healthcare with smarter health plans. Cut expenses by 20-30% with custom solutions. Contact us today at Imagine360.com.

Chapters:

(00:00:00) Intro: TexCap Insurance & Going Up-Market

(00:04:48) Sobriety: It Doesn't Have to Be a "Life Sentence"

(00:09:26) The High-Functioning Trap & Social Lubricant

(00:13:24) Rock Bottom #1: No Insurance During a Crisis

(00:17:27) The Final Wake-Up Call & A Wife's Dream

(00:19:21) The Power of Admitting "I Am an Alcoholic"

(00:28:25) Trading Addiction for Ironman Triathlons

(00:38:30) How to Navigate Happy Hours Sober

(00:45:13) The Blueprint: Steps to Finding Help

Key Links for Social:

@SelfFunded on YouTube for video versions of the podcast and much more - https://www.youtube.com/@SelfFunded

Listen/watch on Spotify - https://open.spotify.com/show/1TjmrMrkIj0qSmlwAIevKA?si=068a389925474f02

Listen on Apple Podcasts - https://podcasts.apple.com/us/podcast/self-funded-with-spencer/id1566182286

Follow Spencer on LinkedIn - https://www.linkedin.com/in/spencer-smith-self-funded/

Follow Spencer on Instagram - https://www.instagram.com/selffundedwithspencer/

"Imagine getting a real-time snapshot of your health just by looking into your phone’s camera for 30 seconds." - Simon

My guests this week are Simon Spurr, Founder of VivaScore, and Chris Burns, a veteran benefits advisor with over 40 years of experience at firms like Mercer and Sequoia. They join the show to demonstrate a piece of technology that feels like science fiction but is actually here today: rPPG (Remote Photoplethysmography).

We discuss how this technology turns a standard smartphone camera into a diagnostic tool capable of measuring blood pressure, heart rate variability (HRV), and stress levels with medical-grade accuracy, no wearables required.

In this episode, we explore whether this "digital avatar" of employee health could become the new front door to primary care. We dive into how employers are using this data to spot "silent killers" like hypertension before they become claims, why engagement rates are hitting 50%+, and how this platform connects the "worried well" to actual care pathways.

Tune in to see how we can finally move from "sick care" to true preventative maintenance, all through an iPhone lens.

Thank you to our 2026 sponsors!

ParetoHealth: ParetoHealth empowers midsize employers with a long-term solution to reduce volatility and lower overall health benefits costs. Visit ParetoHealth.com to learn more.

Samaritan Fund: A program that connects those who need help to the support they need. We are proud to offer the Samaritan Fund Program. Visit SamaritanFundProgram.com to learn more.

Vālenz Health: We're Vālenz Health, your partner in improving health literacy, reducing plan spend, and delivering high-value healthcare. Visit ValenzHealth.com to learn more.

Imagine360: Imagine360 helps self-funded employers save on healthcare with smarter health plans. Cut expenses by 20-30% with custom solutions. Contact us today at Imagine360.com.

Chapters:

(00:00:00) Is This App the Future of Primary Care?

(00:06:12) Global Healthcare: Why Costs Are Rising Everywhere

(00:08:02) Chris Burns: From Mercer to Sequoia to Tech Advisor

(00:12:45) Why Employers are Tired of "Point Solutions"

(00:22:26) How rPPG Technology Works (The Face Scan)

(00:30:18) The "What Next?" Strategy for Employers

(00:39:06) Why Everyone is Talking About HRV (Heart Rate Variability)

(00:44:37) Finding the "Silent Killers" in Your Population

(00:51:46) Gamification: How to Get 50% Engagement

Key Links for Social:

@SelfFunded on YouTube for video versions of the podcast and much more - https://www.youtube.com/@SelfFunded

Listen/watch on Spotify - https://open.spotify.com/show/1TjmrMrkIj0qSmlwAIevKA?si=068a389925474f02

Listen on Apple Podcasts - https://podcasts.apple.com/us/podcast/self-funded-with-spencer/id1566182286

Follow Spencer on LinkedIn - https://www.linkedin.com/in/spencer-smith-self-funded/

Follow Spencer on Instagram - https://www.instagram.com/selffundedwithspencer/